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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Transition Metal-Free Catalyzed Oxidative Coupling of Anilines to Azo Compounds and Thiophenols to Disulfides

Author(s): Vikas Yadav, Mitushree Ghosh and Virendra Prasad*

Volume 27, Issue 5, 2023

Published on: 22 June, 2023

Page: [435 - 443] Pages: 9

DOI: 10.2174/1385272827666230519163647

Price: $65

Abstract

Introduction: Herein we report the efficient oxidative transformations of aryl amines to azoarenes and aryl thiols to the corresponding disulfides using diacetoxyiodobenzene and potassium iodide as transition metal-free catalysts in acetonitrile at room temperature. The developed protocols are highly efficient and employ readily accessible, inexpensive, and environmentally friendly starting.

Methods: All the reactions were carried out in a fuming hood at room temperature (approximately 25- 30°C). The chemicals used in these reactions were purchased from Avra, Aldrich and Spectrochem with a minimum of 95-99% purities and used without further purification.

Results: The reaction of DIB with KI would generate PhI(OAc)I through a partial AcO-I exchange process, and the subsequent reaction of 2PhI(OAc)I with aromatic amines should produce PhNI2 on the elimination of 2AcOH and 2PhI.

Conclusion: The protocol was applicable to a wide range of aromatic amines and aromatic thiols under mild reaction conditions and has no safety concerns, requires inexpensive chemicals and is environmentally friendly.

Keywords: Transition, oxidative, anilines, azo compounds, thiophenols, organic dyes.

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